Open AccessOxetanes from the Ring Contraction of ?-Triflates of ?-Lactones: Oxetane Nucleosides and Oxetane Amino Acids
Author(s) -
Sarah F. Jenkinson,
George W. J. Fleet
Publication year - 2011
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2011.71
Subject(s) - oxetane , chemistry , trifluoromethanesulfonate , ring (chemistry) , stereochemistry , substituent , organic chemistry , catalysis
Alpha-Triflates of gamma-lactones with potassium carbonate in methanol give efficient contraction of the ring to oxetane-1-carboxylates in which the oxygen substituent at C(3) of the oxetane is predominantly trans to the carboxylate at C(2), regardless of the stereochemistry of the starting triflate. The limitations of the procedure are discussed and compared with analogous reactions for the preparation of THF carboxylates. The potential of the contraction in the preparation of oxetane nucleosides (such as oxetanocin) and oxetane sugar amino acids (analogues of oxetin) as peptidomimetics with predisposition to form secondary structural motifs is illustrated.